Synthesis and characterization of some nitrogen heterocycles from d-galactose derivatives |
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Authors: | Andr Augusto Gomes Faraco,Jos Dias De Souza Filho,Maria Auxiliad ra Fontes Prado,Ricardo Jos Alves,Renata Fontes Prado,Norma Beatriz D'Accorso |
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Affiliation: | André Augusto Gomes Faraco,José Dias De Souza Filho,Maria Auxiliadôra Fontes Prado,Ricardo José Alves,Renata Fontes Prado,Norma Beatriz D'Accorso |
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Abstract: | The tetrazoles 5-(6′-acetamido-6′-deoxy-1′,2′:3′,4′-di-O-isopropylidene-D-glycero-α-D-galactohexopyranos-6′-yl)tetrazole ( 1 ) and 5-(6′-acetamido-6′-deoxy-1′,2′:3′,4′–di-O-isopropylidene-L-glycero-α-D-galacto-hexopyranos-6′-yl)-tetrazole ( 2 ) were synthesized by the 1,3-dipolar cycloaddition reaction of the epimeric α-acetamidonitriles 5 and 6 , respectively, with sodium azide. Reaction of tetrazole 1 with acetic anhydride in the presence of pyridine afforded the N-acetyl-1,3,4-oxadiazole derivative 3 and the N-acetylacetamido-1,3,4-oxadiazole derivative 7 . The N-acetylacetamido-1,3,4-oxadiazole derivative ( 8 ) was isolated when the tetrazole 2 was allowed to react under the same conditions. The physical and spectroscopic data of the five new compounds 1, 2, 3, 7 and 8 are presented. |
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